Approach to the core structure of abeo-abietanes and gibberellins via Stork-Danheiser sequence followed by Friedel-Crafts alkylations

作者：Kakde Badrinath N; Bhunia Subhajit; Bisai Alakesh^*

来源：Tetrahedron Letters, 2013, 54(11): 1436-1439.

DOI：10.1016/j.tetlet.2013.01.002

• [6,5,6]-Tricycle
• abeo-Abietanes
• Gibberellins
• Strok-Danheiser sequence
• Friedel-Crafts alkylations

A mild and efficient protocol for the synthesis of [6,5,6]-tricyclic framework (4) of abeo-abietanes (1) and gibberellins (2) via Stork-Danheiser sequence on a bicyclic vinylogous ester followed by Lewis acid-catalyzed Friedel-Crafts alkylations of 3-aryl-2-hydroxymethyl-2-cyclohexenones (5) is developed. A variety of 2-cyclohexenone derivatives (5) underwent smooth Friedel-Crafts alkylations to craft the [6,5,6]-tricyclic skeleton (4) in good to excellent yields.

• 出版日期2013-3-13